can't attach files with Safari

Safari (Mojave 10.14.6.) will not allow me to attach files through Gmail or Yahoo with the paper clip icon. Today is the first time this problem occurred. I have cleared my cache and history. I can attach files only by drag and drop.


I do not have this problem when using Chrome.




MacBook Air 13″, macOS 10.14

Posted on Nov 24, 2020 9:20 PM

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Posted on Jan 8, 2021 2:24 PM

Originally I thought the problem was just with my email, which I have reported about seven times over the past few months. It seems to stem from the November 2020 Security update. Anyway, I am unable to attach anything in my email from Safari, or from other websites (Faxzero, Hartford, among others), so it is obviously a Safari error. How do I know? Because after doing all of the normal clearing cache and all, and still no benefit. I downloaded Firefox at the suggestion from one of the companies mentioned. Although I have only used Safari for years, and did not want to download another browser, I reluctantly did so, and I was able to attache files in each of the three above mentioned companies, as well as others. It is obviously a Safari issue. I am using Mojave 10.14.6 and Safari 14.0.2

60 replies

Dec 6, 2020 11:09 PM in response to rodos2020

Hi rodos2020

If you don't want to upgrade to BigSur then don't, just ignore that update suggestion.

n my case I have an older machine that cannot take Big Sur, the only option I'm given is catalina and I choose to ignore that for the time being (I have 32 bit apps - 32 bit apps are not supported in catalina or Big Sur)


Similarly I choose not to have the box for automatic updates checked. I want the control, but it does mean that I manually look for "other updates" regularly, and install them as needed (and usually do),

hope that helps


Feb 2, 2021 1:53 PM in response to Ticki59

Hello Ticki59, I can assure you this issue is not resolved on either of my Macs using the identical versions of Safari and Gmail.

I have explored the issue, system refreshes and to date I am unable to attach files and/or photos using Gmail file attach or photo attach either as a file or inline. I have also checked with another user using the same specs and the results are the same at this time. Hopefully this issue will resolve as part of a rollout (?).


Feb 18, 2021 3:37 PM in response to Dominic Forbes

Glad to hear of your ability in Yahoo and WeTransfer (not familiar with the product).

As a long time Apple user I use Safari and Apple Mail. Not the most attractive email product I do like the safety albeit there are certainly no guarantees.

Having to move to a new browser of any type seems not only an arduous task but also one that should not be a necessity.

It does appear others as well as you are having luck so I keep my fingers crossed in the hope the fix goes systemwide. There is large world of users suffering the same issue. Apple should be working on this problem a bit more diligently than its current pace.

Considering Apple is consistently adding security measures and promoting Safari as it does, this issue should be on the high priority level.

Being hacked once on Yahoo I shy away completely.

Thanks for the info Dominic.

Bummed it did not work for me.

Frustrating.

Cheers/Be Safe


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can't attach files with Safari

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